Consider southern Delaware. Very nice resort at Sea Colony which has 6 indoor courts, and a moderate climate. Not Florida climate but still nice. No sales taxes, low real estate taxes. I am semi-retired and spend a fair amount of time there. For the two cold months I travel to Naples, or Long Boat Key to get out of the cold.

Best place to retire is a city with good mass transit. As you get on into your retirement, the two things you may no longer be in any condition to do are drive and play tennis. Retiring to a place primarily for tennis is beyond shortsighted; you can play tennis almost anywhere.

Wow,this thread has staying power. Location and climate aside, you might want to pay attention to the prevailing court surfaces in different areas. I live in Southern California and relish any chance I have to travel and play on clay. The hard courts out here (and many of the surfaces at public courts are simply painted cement) really deliver a pounding over time -- and if you plan on having your retirement revolve around tennis, a more benign surface will be important to your aging body and degenerative joints. There is no getting around this.

Actually Southern Delaware sounds pretty good to me, they have clay at Sea Colony, right ? I used to go to Bethany beach back in the day and it was pretty fun, although I've heard it's very crowded now.